Propionic Acid → Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

HRID 502541

반응식

HRID 502541 반응식
[C:1]([OH:5])(=O)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:23]([N:25](CC)CC)C.[NH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:41])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1(C)C=CC=CC=1>[CH3:41][C:34]1[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:31]([NH:30][C:1]([NH:25][CH3:23])=[O:5])[S:32][CH:33]=1

참가 물질

6

반응물 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

생성물 1

HCID 15085569Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of propionic acid (3.8 ml, 50.64 mmol), diphenylphosphoryl azide (10.9 ml, 50.64 mmol), and triethylamine (7.1 ml, 50.64 mmol) in toluene (30 ml) was refluxed for 1 hour. After cooling to room temperature, ethyl 2-amino-4-methylthiophene-3-carboxylate (3.13 g, 16.88 mmol) was added, and the mixture was refluxed for 18 hours. The product was partitioned between ethyl acetate and water, the organic layer washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with ethyl acetate/hexane 1:1, to provide ethyl 4-methyl-2-[(methylamino)carbonylamino]-thiophene-3-carboxylate as pink crystals.

후처리

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for 18 hours
  3. customThe product was partitioned between ethyl acetate and water
  4. washthe organic layer washed with brine
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with ethyl acetate/hexane 1:1

출처 및 근거

ORD 기록
ord-d342891077d542e0be0f599352023051
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776868B2

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